Water → N-(5-Chloro-1,3-benzodithiol-2-ylidene)-1-piperidineethanamine

HRID 2419136ノート

反応式

HRID 2419136 の反応式
[I-].[Cl:2][C:3]1[CH:19]=[CH:18][C:6]2[S:7][C:8](=[N+:10](C)[C:11]3[CH:16]=CC=CC=3)[S:9][C:5]=2[CH:4]=1.NCC[N:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.C(=O)([O-])[O-].[Na+].[Na+].O>CN(C)C=O>[Cl:2][C:3]1[CH:19]=[CH:18][C:6]2[S:7][C:8](=[N:10][CH2:11][CH2:16][N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[S:9][C:5]=2[CH:4]=1

参加物

6

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 33944N-(2-Aminoethyl)piperidineHCID 203138445-Chloro-N-methyl-N-phenyl-1,3-benzodithiol-2-iminium iodide

生成物 1

HCID 20313855N-(5-Chloro-1,3-benzodithiol-2-ylidene)-1-piperidineethanamine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 5-chloro-N-methyl-N-phenyl-1,3-benzodithiol-2-iminium iodide (8.39g), N-(2-aminoethyl)piperidine (2.56g) and anhydrous sodium carbonate (1.06g) in 200 ml of anhydrous dimethylformamide is heated at 120° C under a nitrogen atmosphere for 3 hours. The reaction mixture is poured into 1000 ml of water and extracted with three 300 ml portions of dichloromethane. The combined organic extracts are washed with two 500 ml portions of water, dried over anhydrous sodium sulfate, and concentrated in vacuo to yield an oil. This oil is chromatographed on silica gel (1000 ml) eluting with (1) pentane (1000 ml), (2) chloroform (1000 ml), and finally methanol/chloroform (1:4, 2000 ml). The solid product from elution (3) is recrystallized from pentane to yield 4g of the title compound, melting point 42°-44° C.

後処理

  1. extractionextracted with three 300 ml portions of dichloromethane
  2. washThe combined organic extracts are washed with two 500 ml portions of water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto yield an oil
  6. customThis oil is chromatographed on silica gel (1000 ml)
  7. washeluting with (1) pentane (1000 ml), (2) chloroform (1000 ml), and finally methanol/chloroform (1:4, 2000 ml)
  8. washThe solid product from elution (3)
  9. customis recrystallized from pentane

出典と根拠

ORDレコード
ord-b92fece7341c48f0936c4fd1e0ee8a04
出典データセット
uspto-grants-1978_08
特許番号
US04104467

反応ノート

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